May served as the Director of Communications for the Republican National Committee from 1997 to 2001.[3] In his position, he oversaw activities such as strategic planning, press, radio, television, online services, speech writing, and advertising. He worked as the editor of Rising Tide, the official Republican Party magazine. He also was Vice Chairman of the Republican Jewish Coalition.[5]

After leaving the RNC, he became a director in the Washington, D.C. office of BSMG Worldwide, a public affairs and public relations company. In 2006, he was appointed an adviser to the Iraq Study Group.[5] He strongly dissented from the recommendations that the group came to, and he then worked with various groups to oppose the policies.[6] On July 11, 2008, May was nominated by PresidentGeorge W. Bush to be a member of the Broadcasting Board of Governors for a term expiring August 13, 2009. "In this very challenging period of history, it is vital that the United States communicates with audiences abroad clearly and creatively,” May said, “I will be honored and privileged if I can assist with this mission.”[7]

May is an International Patron of the Henry Jackson Society.[1] In October 2007, The Daily Telegraph named May number 94 in its list of the '100 most influential conservatives in America'. The paper labeled him "an outspoken proponent of the need to achieve victory in Iraq and the broader war against Muslim extremism". It also described him as a "nimble" Republican Party activist in the American media.[4]

He also told Smiley, "I'm rooting for the guy in the White House, personally, 'cause I do think he has done a good job".[2] In the aftermath of the American re-deployment in Iraq during July 2009, he wrote for The Washington Times, "[t]he news is not that American combat troops withdrew from Iraqi cities. The news is that American combat troops withdrew from Iraqi cities in victory-- rather than in defeat."[6]

May wrote for the San Angelo Standard Times in October 2012 that, despite the death of Osama bin Laden and other successes against al-Qaida, he considered the group "degraded" but not actually "defeated". He referred to the attempted assassination of Malala Yousufzai as a particular sign of a still dangerous Taliban. He argued,

"Roosevelt and Churchill grasped what too many analysts in government, academia, media and think tanks do not: To prevail against America's 21st century enemies, kinetic warfare is necessary but insufficient. An ideological war, a war of ideas, also must be waged. And on that front, we have not yet begun to fight."[11]

During the beginning of the CIA leak scandal, May wrote in September 2003 that an ex-administration official had told him that Valerie Plame was a CIA agent, and May stated that the fact was an open secret widely known across Washington, D.C. He also remarked that he chose not to mention this in his own writings since he considered this to be irrelevant to anything else.[12]David Corn, writing for The Nation in March 2007 in the aftermath of the scandal, disputed May's assertions, and he quoted Plame as saying that only a handful of people knew about her covert status. Corn then called upon May, along with other conservative commentators such as Jonah Goldberg who had made similar statements, to apologize.[13]

On December 31, 2009, May jokingly suggested releasing detainees from Guantanamo Bay to Yemen, then sending "missiles to strike the baggage-claim area".[18] He later defended the remarks, describing critics such as Greenwald as "humorless". He also stated that he had intended to highlight the logical disconnect between someone both supporting the extrajudicial killing of suspected militants and opposing the holding of suspected militants at Guantanamo Bay at the same time.[19]